Polyoxyalkylene triamine is widely used as a curing agent for epoxy resin, or a raw material of polyamides. As the process for producing the same, there is known a process of using a catalyst to cause the corresponding polyoxyalkylene triol as a raw material to react directly with ammonia and hydrogen. It is generally considered that in this direct amination reaction using the polyoxyalkylene triol as a raw material, the reaction advances along the step (1) of the generation of aldehyde and/or ketone groups by dehydrogenation from the hydroxyl groups, the step (2) of the addition of ammonia, the step (3) of the generation of imino groups by dehydration, and the step (4) of the conversion of the imino groups to amino groups by the addition of hydrogen. In order to improve the reactivity and selectivity in the successive steps, there has been suggested a catalyst containing a nickel component, or some other catalyst as a catalyst for catalytic reduction.
For example, U.S. Pat. No. 3,347,926 discloses a process of using a Raney(sponged) nickel catalyst into which a small amount of chromium is incorporated to produce an aliphatic amine from a raw material containing hydroxyl groups. In JP-B 1-40048, polyoxyalkylene diol is caused to react in the presence of an ordinary Raney(sponged) nickel catalyst. GB-B 2175910 describes a circulating-manner process for producing polyoxyalkylene diamine using a Raney(sponged) nickel catalyst to which molybdenum is added. EP-A 81701 and U.S. Pat. No. 4,774,263 discloses reaction of polyoxyalkylene triol having a molecular weight of 6000 in the presence of a Raney(sponged) nickel catalyst.
In the meantime, EP-A 356047 and JP-A 7-3009 disclose processes of using a catalyst on which two or more kinds of ruthenium and other transition metals are carried to produce polyoxyalkylene diamine.
JP-B 49-14158 and JP-B 49-14159 disclose reaction between a propylene oxide polymer and ammonia using a carbon catalyst on which ruthenium is carried.